Chloroform → 90595-44-1

To a solution of 4-cyanobenzaldehyde (0.86 g, 6.6 mmol) in ethanol (15 ml) was added a solution of cysteamine HCl (0.5 g, 4.4 mmol) in water (5 ml) and the solution stirred at RT for 18 h. The bulk of the ethanol was removed by rotary evaporator and the residue was treated with water (15 ml) and extracted with diethyl ether (3×20 ml) to remove excess aldehyde. The aqueous layer was basified with solid sodium carbonate (0.3 g) resulting in the formation of an oil. The mixture was extracted with ether (2×25 ml), washed with brine (1×50 ml), dried (MgSO4) and evaporated to give a clear oil that solidified on standing (0.62 g). Column chromatography (silica gel, 100% chloroform) afforded pure 4-(1,3-thiazolidin-2-yl)benzonitrile (6) (0.56 g, 67%) as clear oil that solidified on standing, mp 57-58°. 1H nmr (CDCl3, 300 MHz) 3.05-3.15, m, H4,4; 3.2-3.35, m, H5; 3.4-3.5, m, H5; 5.64, s, H2; 7.63, app. s, H2′,3′,5′,6′. ESI (+ve) MS m/z 191 (M+H, 100%).

1. customThe bulk of the ethanol was removed by rotary evaporator
2. additionthe residue was treated with water (15 ml)
3. extractionextracted with diethyl ether (3×20 ml)
4. customto remove excess aldehyde
5. customresulting in the formation of an oil
6. extractionThe mixture was extracted with ether (2×25 ml)
7. washwashed with brine (1×50 ml)
8. dry with materialdried (MgSO4)
9. customevaporated
10. customto give a clear oil that solidified

ORD record

ord-0d8215ac021e4a96a4323e26d8bd07a8

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863313B2